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Electron-accepting compound and composition for charge-transporting film, and luminescent element using same

a charge-transporting film and electron-accepting compound technology, applied in the direction of organic compounds of group 3/13 elements, identification means, instruments, etc., can solve the problems of increasing the demand for organic electroluminescent elements, reducing the operating voltage, and increasing the operating voltage at continuous operation. , to achieve the effect of excellent thermal stability, high hole injection/transporting ability, and excellent thermal stability

Active Publication Date: 2019-01-17
MITSUBISHI CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a composition for a charge-transporting film that contains an electron-accepting compound and a charge-transporting compound. This composition exhibits excellent thermal stability and high hole injection / transporting ability. Additionally, the invention provides an organic electroluminescent element that contains the electron-accepting compound in a layer between the anode and the cathode or the luminescent layer. This element exhibits excellent thermal stability and is operable at low voltage and high efficiency with excellent operation stability. The invention also provides a charge-transporting ion compound that is stable thermodynamically and electrochemically with small interaction with the cation, and the formed charge-transporting film shows excellent heat resistance and high hole injection / transporting ability. The organic electroluminescent element containing the charge-transporting ion compound exhibits excellent heat resistance, can operate at low voltage and high efficiency, and has exceptional operation stability.

Problems solved by technology

However, though the luminescent efficiency is improved, a big problem for expanding the demand for the organic electroluminescent element is a decrease in operating voltage.
Also, in general uses other than the portable uses, the cost of operating IC (Integrated Circuit) depends on the operating voltage and lower operating voltage results in a lower cost.
Moreover, a gradual increase in the operating voltage at continuous operation is also a big problem for maintaining stable display properties of the display element.

Method used

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  • Electron-accepting compound and composition for charge-transporting film, and luminescent element using same
  • Electron-accepting compound and composition for charge-transporting film, and luminescent element using same
  • Electron-accepting compound and composition for charge-transporting film, and luminescent element using same

Examples

Experimental program
Comparison scheme
Effect test

synthetic example 1

Synthesis of (B-1)

[0276]Cumyltolyliodonium chloride (26 g) was added to a methylene chloride (900 ml) solution of lithium tetrakis(nonafluorobiphenyl)boron (89.5 g) and the whole was reacted at room temperature for 5 hours. The methylene chloride layer was washed with purified water several times and, after treated with active carbon, was concentrated under reduced pressure. The residue was recrystalized to obtain an objective substance (B-1) (31 g).

[0277]The structure of the synthesized compound was identified by MS analysis and NMR. The measurement conditions for the MS analysis are as follows.

[0278]Measurement conditions for MS analysis: ionization method: ESI (+ / −)

[0279]Cation: C16H18I+ (337.0)

[0280]Anion: C48BF36− (1271.0)

synthetic example 2

Synthesis of (B-18)

[0281]A mixed solution of 3-bicyclo[4.2.0]octa-1,3,5-trieneboronic acid (30.3 g), 1,4-dibromo-2,3,5,6-tetrafluorobenzene (125.9 g), 1,2-dimethoxyethane (1 L), and a 2.0M aqueous tripotassium phosphate solution (0.26 L) was deaerated with argon. Thereafter, tetrakistriphenylphosphine palladium(0) (7.3 g) was added thereto and the whole was heated and stirred at an inner temperature of 73° C. for 7.5 hours.

[0282]After cooling to room temperature, purified water (0.25 L) was added and extraction was performed with toluene (1.8 L). After the organic layer was washed sequentially with purified water (0.5 L) and saturated aqueous sodium chloride solution (0.5 L), the layer was dried with anhydrous magnesium sulfate and filtrated and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain 3-(4-bromo-2,3,5,6-tetrafluorophenyl)bicyclo[4.2.0]octa-1,3,5-triene (45.5 g).

[0283]Under an argon stream, a dry diethyl ether (760 mL) sol...

synthetic example 3

Synthesis of (B-20)

[0285]Under an argon stream, 4-isopropyl-4′-methyldiphenyliodonium chloride (4.24 g, 1.00 eq.) was slowly charged portionwise at an inner temperature of 8° C. under stirring into a methanol (330 mL) solution of lithium tetrakis(4′-(1,2-dihydrocyclobuta[a]naphthalen-4-yl)-2,2′,3,3′,5,5′,6,6′-octafluoro-1,1′-biphenyl-4-yl)borate (25.6 g) and dichloromethane (80 mL). After stirring at an inner temperature of 8 to 9° C. for 2 hours, methanol was distilled off under reduced pressure. The residue was again dissolved in dichloromethane (150 mL) and, after inorganic salts were filtrated off, the filtrate was concentrated.

[0286]The residue was purified by silica gel column chromatography (hexane / dichloromethane=1 / 2 to 1 / 4) to obtain an objective substance (B-20) (20.9 g, yield 85.6%). The structure of the synthesized compound was identified by NMR.

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Abstract

The present invention provides with an electron-accepting compound having a structure of the following formula (1):

Description

TECHNICAL FIELD[0001]The present invention relates to an electron-accepting compound and a composition for a charge-transporting film, and a charge-transporting film and an organic electroluminescent element using the same. Specifically, it relates to an excellent composition for a charge-transporting film and an electron-accepting compound, which can afford an organic electroluminescent element having excellent heat resistance and capable of operating at low voltage and also relates to a charge-transporting film using the same and a method for manufacturing the same. Further, it relates to an organic electroluminescent element using the same.BACKGROUND ART[0002]In recent years, as electroluminescent (electroluminescence: EL) elements, electroluminescent elements employing organic materials (organic electroluminescent elements) in place of inorganic materials such as ZnS. In the organic electroluminescent element, high luminescent efficiency thereof is one important factor but the l...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01L51/00C08L65/02H01L51/50H01L51/52H10K99/00
CPCH01L51/0051H01L51/0059C08L65/02H01L51/0096H01L51/5084H01L51/001H01L51/5221H01L51/5012H01L51/5092C08L2203/20C08L2312/00H01L51/5056C07F5/027B05D7/24B05D3/0254C09K11/06C09K2211/1014C09K2211/1007C09K2211/1011H10K85/615H10K85/626H10K50/15H10K50/17H10K71/00H10K85/322H10K71/164C08G2261/135C08G2261/312C08G2261/314C08G2261/3162C08G2261/76C08G2261/91C08L2205/02H10K85/111H10K85/622C09D165/00C08L65/00H10K85/649H10K85/631G09F9/30H10K85/611H10K50/11H10K50/82H10K50/167H10K50/171H10K77/10
Inventor GOROHMARU, HIDEKIOKABE, KAZUKIIIDA, KOICHIROUMEMOTO, TOMOKAZUBANDO, YOSHIMASAISHIBASHI, KOICHIKAJIYAMA, YOSHIKOABE, TOMOHIRO
Owner MITSUBISHI CHEM CORP
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